键合型手性固定相的研究进展

陈娇 石浩

引用本文: 陈娇,  石浩. 键合型手性固定相的研究进展[J]. 色谱, 2017, 35(12): 1229-1239. doi: 10.3724/SP.J.1123.2017.09017 shu
Citation:  CHEN Jiao,  SHI Hao. Research progress of bonded chiral stationary phases[J]. Chinese Journal of Chromatography, 2017, 35(12): 1229-1239. doi: 10.3724/SP.J.1123.2017.09017 shu

键合型手性固定相的研究进展

  • 基金项目:

    浙江省自然科学基金项目(LY13B020013).

摘要: 手性分离在生物医药等领域具有重要意义。高效液相色谱(HPLC)因其经济、快速、高效等特点被广泛应用于手性化合物的分离分析中。手性固定相(CSP)是HPLC实现手性分离的核心,而制备有效CSP的关键在于手性选择剂的筛选。近年来,大量文献报道了新型CSPs的制备,其中键合型CSPs因具有溶剂耐受性和较高稳定性等优点受到了广泛关注。该文对近年来以手性单分子、多糖、环糊精、大环抗生素、冠醚、杯芳烃及生物碱等为手性选择剂制备的新型键合型CSPs进行了归纳整理,并对其发展前景进行了展望。

English

    1. [1] Thompson R. J Liq Chromatogr Relat Technol, 2005, 28(7/8):1215

    2. [2] Cancelliere G, D'Acquarica I, Gasparrini F, et al. J Sep Sci, 2006, 29(6):770

    3. [3] Beesle T E. LC GC Europe, 2011, 24(5):270

    4. [4] Pirkle W H, Pochapsky T C. Chem Rev, 1989, 89:347

    5. [5] Weng X L, Bao Z B, Luo F, et al. Progress in Chemistry, 2014, 26(2):413翁西伦, 鲍宗必, 罗飞, 等. 化学进展, 2014, 26(2):413

    6. [6] Lämmerhofer M. J Chromatogr A, 2010, 1217:814

    7. [7] Pirkle W H, Hyun M H, Tsipouras A, et al. Pharm Biomed Anal, 1984, 2:173

    8. [8] Wolf C, Pirkle W H. J Chromatogr A, 1998, 799:177

    9. [9] Blum A M, Lynam K G, Nicolas E C. Chirality, 1994, 6:302

    10. [10] Fernaneds C, Tiritan M, Pinto M. Chromatographia, 2013, 76(15/16):871

    11. [11] Moiteiro C, Fonseca N, Curto M J M, et al. Tetrahedron:Asymmetry, 2006, 17(23):3248

    12. [12] Wang D-C, Luo J, Yao S, et al. EDP Science, 2016, 39(1):3

    13. [13] Liu G Q, Zhan F P, Lin A Q, et al. Applied Chemical Industry, 2011, 40(3):402刘国庆, 詹峰萍, 林爱清, 等. 应用化工, 2011, 40(3):402

    14. [14] Yu J, Lee J M, Ryoo J J. Chirality, 2016, 28(4):276

    15. [15] Yu J, Dong H R, Lee J M, et al. Chirality, 2016, 28(3):186

    16. [16] Yu J J, Hyun M H, Armstrong D W, et al. Bull Korean Chem Soc, 2015, 36(2):723

    17. [17] Li Y, Li L J, Jiang D G, et al. Chemical Reagents, 2016, 38(9):829李杨, 李连杰, 蒋登高, 等. 化学试剂, 2016, 38(9):829

    18. [18] Shen J, Ikai T, Okamoto Y. J Chromatogr A, 2014, 1363:51

    19. [19] Shen J, Okamoto Y. Chem Rev, 2016, 116(3):1094

    20. [20] Oliveros L, Senso A, Franco P, et al. Chirality, 1998, 10(4):283

    21. [21] Garcés J, Franco P, Oliveros L, et al. Tetrahedron:Asymmetry, 2003, 14(9):1179

    22. [22] Okamoto Y, Yashima E. Chem Inform, 1998, 29(28):1020

    23. [23] Chankvetadze B. J Chromatogr A, 2012, 1269:26

    24. [24] Ikai T, Okamoto Y. Chem Rev, 2009, 109(11):6077

    25. [25] Shen J, Okamoto Y. Chem Rev, 2016, 116(3):1094

    26. [26] Chen X M, Yamamoto C, Okamoto Y. J Chromatogr A, 2006, 1104:62

    27. [27] Tang S, Ikai T, Tsuji M, et al. J Sep Sci, 2010, 33(9):1255

    28. [28] Shen J, Liu S Y, Shen X D, et al//Okamoto Y. Chinese National Symposium on Molecular Chiral and 2011 Green Chiral Forum, Hangzhou, 2011:105沈军, 刘双燕, 沈贤德, 等//冈本佳男. 全国分子手性学术研讨会暨2011绿色手性论坛, 杭州, 2011:105

    29. [29] Shen J, Ikai T, Shen X, et al. Chem Let, 2010, 39(5):442

    30. [30] Shen J, Li P, Liu S, et al. Chirality, 2011, 23(10):878

    31. [31] Shen J, Liu S, Li P, et al. J Chromatogr A, 2012, 1246:137

    32. [32] Tu H S, Fan J, Tan Y, et al. Chinese Journal of Chromatography, 2014, 32(5):452涂鸿盛, 范军, 谭艺, 等. 色谱, 2014, 32(5):452

    33. [33] Tan Y, Fan J, Lin C, et al. J Sep Sci, 2014, 37(5):488

    34. [34] Li Y, Feng H, Jiang D G. Chinese Journal of Chromatography, 2016, 34(8):739李杨, 封华, 蒋登高. 色谱, 2016, 34(8):739

    35. [35] Zhang X L, Zhang W J, Wang L T, et al. Chinese Journal of Analysis Laboratory, 2016, 35(5):497张晓莉, 张文娟, 王利涛, 等. 分析试验室, 2016, 35(5):497

    36. [36] Lin Y Z, Zhou J, Tang J, et al. Chinese Journal of Chromatography, 2016, 34(1):96林宇洲, 周杰, 唐建, 等. 色谱, 2016, 34(1):96

    37. [37] Huang T B, Long Y D, Wang H. Chinese Journal of Chromatography, 1993, 11(2):81黄天宝, 龙远德, 王红. 色谱, 1993, 11(2):81

    38. [38] Shen H M, Ji H B, Wu H K. Chinese Journal of Organic Chemistry, 2014, 34(8):1549沈海民, 纪红兵, 武宏科, 等. 有机化学, 2014, 34(8):1549

    39. [39] Zhou Z M, Li X, Chen X P, et al. Talanta, 2010, 82(2):775

    40. [40] Xia Y, Ng S C, Tan T T, et al. J Chromatogr A, 2012, 1269:52

    41. [41] Li L, Chen B, Zhou R, et al. Talanta, 2017, 174:179

    42. [42] Zhou J, Wang Y Z, Zhang Z Z. Chinese Journal of Applied Chemistry, 2009, 26(3):355周婕, 王艳芝, 张振中. 应用化学, 2009, 26(3):355

    43. [43] Zhou J, Pei W, Zheng X, et al. J Chromatogr Sci, 2015, 53(5):676

    44. [44] Zhou J, Sun F, Du Q, et al. J Chromatogr Sci, 2016, 54(3):43

    45. [45] Varga G, Tarkanyi G, Nemeth K, et al. J Pharm Biomed Anal, 2010, 51(1):84

    46. [46] Varga G, Fodor G, Ilisz I, et al. J Pharm Biomed Anal, 2012, 70:71

    47. [47] Pang L, Zhou J, Tang J, et al. J Chromatogr A, 2014, 1363:119

    48. [48] Lin Y Z, Zhou J, Tang W H. Chinese Journal of Chromatography, 2016, 34(1):96林宇洲, 周杰, 唐卫华. 色谱, 2016, 34(1):96

    49. [49] Ma H P, Li L S, Chen H M, et al. Chinese Jouernal of Analytical Chemistry, 2010, 38(2):158马海萍, 李来生, 陈会明, 等. 分析化学, 2010, 38(2):158

    50. [50] Li L S, Ma H P, Fang Y S, et al. Chinese Journal of Analysis Laboratory, 2011, 30(11):20李来生, 马海萍, 方奕珊, 等. 分析试验室, 2011, 30(11):20

    51. [51] Li L S, Zhou R D, Cheng B P, et al. Journal of Nanchang University (Natural Science), 2013, 37(2):145李来生, 周仁丹, 程彪平, 等. 南昌大学学报(理科版), 2013, 37(2):145

    52. [52] Li L S, Zhou R D, Cheng B P, et al. Journal of Nanchang University (Natural Science), 2013, 37(3), 233李来生, 周仁丹, 程彪平, 等. 南昌大学学报(理科版), 2013, 37(3):233

    53. [53] Cheng B P, Li L S, Zhou R D, et al. Chinese Journal of Chromatography, 2014, 32(11):1219程彪平, 李来生, 周仁丹, 等. 色谱, 2014, 32(11):1219

    54. [54] Zhou R D, Li L S, Cheng B P, et al. Chemical Journal of Chinese Universities, 2014, 35(6):1152周仁丹, 李来生, 程彪平, 等. 高等学校化学学报, 2014, 35(6):1152

    55. [55] Cheng B P, Li L S, Zhou R D, et al. Chemical Journal of Chinese Universities, 2015, 36(5):872程彪平, 李来生, 周仁丹, 等. 高等学校化学学报, 2015, 36(5):872

    56. [56] Cheng B P, Li L S, Zhou R D, er al. Journal of Nanchang University (Natural Science), 2017, 41(1):77程彪平, 李来生, 周仁丹, 等. 南昌大学学报(理科版), 2017, 41(1):77

    57. [57] Zeng C, Li L S, Cheng B P, et al. Chinese Journal of Chromatography, 2016, 34(3):314曾春, 李来生, 程彪平, 等. 色谱, 2016, 34(3):314

    58. [58] Gasparrini F, D'Acquarica I, Misit D, et al. Pure & Appl Chem, 2003, 75(2/3):407

    59. [59] Armstrong D W, Tang Y, Chen S, et al. Anal Chem, 1994, 66(9):1473

    60. [60] Ilisz I, Berkecz R, Péter A. J Chromatogr A, 2009, 1216:1845

    61. [61] Ward T J. J Chromatogr A, 2001, 906:73

    62. [62] Ding G S, Huang X J, Liu X L, et al. Chinese Journal of Chromatography, 2002, 20(6):519丁国生, 黄晓佳, 刘学良, 等. 色谱, 2002, 20(6):519

    63. [63] Zhang S Q, He S H. Chemical Reagents, 2013, 35(5):427张淑琼, 何树华. 化学试剂, 2013, 35(5):427

    64. [64] Staroverov S M, Kuznetsov M A, Nesterenko P N, et al. J Chromatogr A, 2006, 1108:263

    65. [65] Zhang D T, Cai X J, Xu X Z. Chinese Journal of Analytical Chemistry, 2008, 36(6):849张大同, 蔡小军, 徐秀珠. 分析化学, 2008, 36(6):849

    66. [66] Lei W, Zhang L Y, Zhu Y X, et al. Chinese Jouernal of Analytical Chemistry, 2010, 38(11):1544雷雯, 张凌怡, 朱亚仙, 等. 分析化学, 2010, 38(11):1544

    67. [67] Pérez-Quintanilla D, Morante-Zarcero S, Sierra I. J Colloid Interface Sci, 2014, 414(4):14

    68. [68] Abdollahpour A, Heydari R, Shamsipur M. AAPS Pharm Sci Tech, 2016, 18(5):1855

    69. [69] Tan G, Xue J Y, Hyun M H. J Sep Sci, 2006, 29(10):1407

    70. [70] Mohammadzadeh K R. J Inclusion Phenom Macrocyclic Chem, 2012, 75(1/2):11

    71. [71] Hyun M H. J Sep Sci, 2003, 26(3/4):242

    72. [72] Hyun M H. Chirality, 2015, 27(9):576

    73. [73] Cho H S, Choi H J, Hyun M H. J Chromatogr A, 2009, 1216:7446

    74. [74] Hyun M H, Jin J S, Lee W. J Chromatogr A, 1998, 822:155

    75. [75] Hyun M H. J Liq Chromatogr Related Technol, 2007, 30(5/7):853

    76. [76] Agneeswari R, Sung J Y, Jo E S, et al. Molecules, 2016, 21(8):1051

    77. [77] Kupai J, Lévai S, Antal K, et al. Tetrahedron:Asymmetry, 2012, 23(6/7):415

    78. [78] Zhao J, Wu H, Wang D, et al. J Sep Sci, 2015, 38(22):291

    79. [79] Wu H X, Wang D Q, Zhao J C, et al. Chinese Journal of Chromatography, 2016, 34(1):62吴海霞, 王东强, 赵见超, 等, 色谱, 2016, 34(1):62

    80. [80] Gutsche C D, Rogers J S, Stewart D. Pure & Appl Chem, 1990, 62(3):485

    81. [81] Gebauer S, Friebe G, Scherer G, et al. J Chromatogr Sci, 1998, 36(8):388

    82. [82] Lee Y K, Ryu Y K, Ryu J W, et al. Chromatographia, 1997, 46(9/10):507

    83. [83] Hu K, Zhao W, Wen F, et al. Talanta, 2011, 85(1):317

    84. [84] Schneider C, Menyes U, Jira T. J Sep Sci, 2010, 33(19):2930

    85. [85] Wang Z, Yin D D, Wang X L, et al. Chinese Journal of Pharmaceutical Analysis, 2015, 35(7):1127王转, 尹东东, 王杏林, 等. 药物分析杂志, 2015, 35(7):1127

    86. [86] Tan H M, Soh S F, Zhao J, et al. Chirality, 2011, 23(1):91

    87. [87] Karol K, Jacek G. Cheminform, 2010, 41(39):421

    88. [88] Kacprzak K, Gawronski J. Synthesis, 2001, 32(34):961

    89. [89] Tian S K, Chen Y, Hang J, et al. Acc Chem Res, 2004, 37(8):621

    90. [90] Lämmerhofer M, Lindner W. J Chromatogr A, 1996, 741:33

    91. [91] Mandl A, Nicoletti L, Lämmerhofer M, et al. J Chromatogr A, 1999, 858:1

    92. [92] Ilisz I, Gecse Z, Pataj Z, et al. J Chromatogr A, 2014, 1363:169

    93. [93] Lajko G, Orosz T, Grecso N, et al. Anal Chim Acta, 2016, 921:84

    94. [94] Lajko G, Grecso N, Toth G, et al. Chirality, 2017, 29(6):225

    95. [95] Kacprzak K M, Maier N M, Lindner W. Tetrahedron Lett, 2006, 47(49):8721

    96. [96] Kacprzak K M, Lindner W. J Sep Sci, 2011, 34(18):2391

    97. [97] Sykora D, Vozka J, Tesarova E, et al. Electrophoresis, 2017, 38:1956

    98. [98] Song J F, Feng S W, Xu X D, et al. Chinese Journal of Chromatography, 2016, 34(1):74宋佳枫, 冯四伟, 徐晓冬, 等. 色谱, 2016, 34(1):74

    99. [99] Blaschke G. J Liq Chromatogr, 1986, 9(2/3):341

    100. [100] Zhong Q, Han X, He L, et al. J Chromatogr A, 2005, 1066:55

    101. [101] Payagala T, Wanigasekara E, Armstrong D W. Anal Bioanal Chem, 2011, 399(7):2445

    102. [102] Bai J W, Shen X D, Liu W B, et al. Acta Polym Sin, 2013, 13(4):419

    103. [103] Okamoto Y, Hatada K. J Liq Chromatogr, 1986, 9(2/3):369

    104. [104] Lee Y K, Hisamitsu N, Onimura K, et al. Polym J. 2002, 34(1):9

    105. [105] Yashima E, Matsushima T, Nimura T. et al. Korea Polym J, 1996, 4(2):139

    106. [106] Zhang C, Wang H, Geng Q, et al. Macromolecules, 2013, 46(21):8406

    107. [107] Kunieda N, Chakihara H, Kinoshita M. Chem Lett, 1990, 26(38):317

    108. [108] Gao H J, Isobe Y, Onimura K, et al. Polym J, 2007, 39(8):764

    109. [109] Tsuchida A, Hasegawa T, Kobayashi K, et al. Bull Chem Soc Jpn, 2002, 75(12):2681

    110. [110] Tamura K, Miyabe T, Iida H, et al. Polym Chem, 2011, 2(1):91

    111. [111] Yashima E, Maeda K, Iida H, et al. Chem Rev, 2009, 109(11):6102

    112. [112] Sung J Y, Choi S H, Hyun M H. Chirality, 2016, 28(3):253

    113. [113] Gasparrini F, Misiti D, Marco P A, et al. Organic Letters, 2002, 4(23):3993

    114. [114] Ema T, Tanida D, Sugita K, et al. Organic Letters, 2008, 10(12):2365

  • 加载中
计量
  • PDF下载量:  3
  • 文章访问数:  824
  • HTML全文浏览量:  57
文章相关
  • 收稿日期:  2017-09-08
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章